Stereoselective Synthesis of C13–C28 Fragment of Marinomycin A

Abstract

Synthesis of the C13–C28 fragment of marinomycin A, consisting of all the five stereocenters, was achieved by asymmetric synthesis, starting from l-malic acid. The simple convergent approach utilized cross metathesis of two key olefinic fragments for the introduction of the C20–C21 double bond. Two of the five stereocenters, C19 and C27, were realized from l-malic acid, while, C17 and C23 are introduced by Sharpless asymmetric epoxidation and C25 by a selective allylation reaction.

Key words

marinomycins - stereoselective - cross-metathesis - Hoveyda–Grubbs

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